Squaric acid has a pKa of 1.5, making it much more acidic than many carboxylic acids (typical pKa values of 4–5). One of the reasons for its acidity is resonance stabilization of its conjugate base, which is shown below. Add curved arrows to the structure on the left to show how it is converted to the other resonance contributor shown to the right.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
Section: Chapter Questions
Problem 9E
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Squaric acid has a pKa of 1.5, making it much more acidic than many carboxylic acids (typical pKa values of 4–5). One of the reasons for its acidity is resonance stabilization of its conjugate base, which is shown below. Add curved arrows to the structure on the left to show how it is converted to the other resonance contributor shown to the right.

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